Chloroacetyl chloride → Ethyl 2-(chloromethyl)-1,3-benzoxazole-5-carboxylate

HRID 465046ノート

反応式

HRID 465046 の反応式
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-])=O.[Cl:16][CH2:17][C:18](Cl)=O.P(Cl)(Cl)(Cl)=O>[Ni].C(O)C>[Cl:16][CH2:17][C:18]1[O:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N:13]=1

参加物

6

反応物 3

HCID 6577Chloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 87895Benzoic acid, 4-hydroxy-3-nitro-, ethyl ester

生成物 1

HCID 15211498Ethyl 2-(chloromethyl)-1,3-benzoxazole-5-carboxylate

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

Ethyl 4-hydroxy-3-nitrobenzoate (32 g) prepared according to the method described in J. Org. Chem., vol. 26, p. 2223 (1961) was subjected to reduction under increased pressure at 70 atm in the presence of a Raney Nickel catalyst in absolute ethanol (200 ml). The product was then caused to react with chloroacetyl chloride, and was subsequently subjected to ring closure with phosphorous oxychloride to yield 2-chloromethyl-5-ethoxycarbonylbenzoxazole (27.3 g). The chloromethyl compound (10 g) was caused to react with dimethylamine to yield 2-dimethylaminomethyl-5-ethoxycarbonylbenzoxazole (6 g), which was subsequently subjected to reduction with lithium aluminium hydride in anhydrous tetrahydrofuran (60 ml) thereby to obtain 2-dimethylaminomethyl-5-hydroxymethylbenzoxazole (2 g).

出典と根拠

ORDレコード
ord-f637b528364845b0bd11923a64889953
出典データセット
uspto-grants-1985_10
特許番号
US04550118

反応ノート

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